4-(Dodec­yloxy)benzonitrile

Huey Chong Kwong; Mohamad Zaki Ab Rahman; Mohamed Ibrahim Mohamed Tahir; Sidik Silong

doi:10.1107/S1600536811041602

. 2011 Oct 22;67(Pt 11):o3000. doi: 10.1107/S1600536811041602

4-(Dodecyloxy)benzonitrile

Huey Chong Kwong ^a, Mohamad Zaki Ab Rahman ^a, Mohamed Ibrahim Mohamed Tahir ^a, Sidik Silong ^a,^*

PMCID: PMC3247400 PMID: 22220018

Abstract

In the title compound, C₁₉H₂₉NO, the C—C and C—N bond distances of the benzonitrile group are 1.445 (2) and 1.157 (2) Å, respectively. The aliphatic fragment adopts a bent zigzag arangement which differs from the planar zigzag arrangement normally observed in n-alkanes or long-chain alkylbenzenes. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds occur. A C—H⋯N interaction also occurs. In the crystal, molecules are packed with the nitrile and aliphatic groups oriented in a head-to-tail fashion involving, forming a ripple-like motif along the a axis.

Related literature

For standard bond lengths, see Allen et al. (1987 ▶). For related structures, see: Merz (2002 ▶); Britton et al. (2004 ▶); Kwong et al. (2011 ▶); Boese et al. (1999 ▶). The title compound was synthesised by reacting hydroxybenzonitrile with bromoalkane, see Rahman et al. (2009 ▶).

Experimental

Crystal data

C₁₉H₂₉NO
M _r = 287.45
Monoclinic,
a = 5.7080 (6) Å
b = 7.3644 (8) Å
c = 40.642 (5) Å
β = 90°
V = 1708.4 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.52 mm⁻¹
T = 100 K
0.17 × 0.14 × 0.09 mm

Data collection

Oxford Diffraction Gemini E diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 ▶) T _min = 0.930, T _max = 0.955
9444 measured reflections
3214 independent reflections
2575 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.127
S = 0.98
3202 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: Gemini (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: CRYSTALS.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811041602/kp2353sup1.cif

e-67-o3000-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041602/kp2353Isup2.hkl

e-67-o3000-Isup2.hkl^{(201.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811041602/kp2353Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H102⋯N7ⁱ	0.98	2.67	3.468 (2)	139
C3—H31⋯O1ⁱⁱ	0.94	2.67	3.569 (5)	159

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors would like to acknowledge the Ministry of Science, Technology and Innovation (MOSTI) Malaysia for funding (Research Grant Nos. 04–01–04-SF0144 and 05–02–10–0934RU).

supplementary crystallographic information

Comment

The titled compound (I), 4-(dodecyloxy)benzonitrile (Fig. 1) was synthesised by reacting hydroxybenzonitrile with bromoalkane (Rahman et al., 2009). Bond distance and angles of (I) are in normal range (Allen et al. 1987). Bond distance of the benzonitrile group C5—C6 and C6—N7 are 1.445 (2) Å and 1.157 (2) Å, respectively and these bond lengths are comparable with those in p-decylbenzonitrile of 1.446 (3) Å and 1.153 (3) Å, respectively (Britton et al., 2004).

In this molecule, the plane formed by benzonitrile ring and O1 was almost planar, the largest deviation from the least-squares plane is 0.0187 (12) Å at O1. The benzene ring and the alkane carbon skeleton (C9—C2—O1—C10) form the torsion angle of 1.62 (2)°. In this structure the alkane carbon skeleton has a bended zigzag arrangement; this arrangement is in agreement with previously reported alkoxy benzenen [4-hexyloxybenzamide, Kwong et al., 2011] However, the mean C(H3)—C(H2) and C(H2)—C(H2) distances, and C(H3)—C(H2)—C and C(H2)—C(H2)—C angles, are in accordance of those determined for n-alkanes and long-chain alkylbenzene, 1.521 (1) Å and 112.8 (1)–113.5 (1)°, respectively. (Boese et al., 1999; Merz, 2002; Britton et al., 2004).

In the crystal packing, the centrosymmetric hydrogen bond C3—H31···O1 is formed generating a hydrogen bonded ring (Table 1 and Fig. 2). Packing of the titled compound shows a ripple-like motif (Fig. 2) with nitrile and aliphatic groups oriented head-to-tail. The stacking interaction between the aromatic rings with the separation distances of their centres of gravity Cg1···Cg1ⁱ (-x,1-y,1-z) of 3.573 (1) and Cg1···Cg1ⁱⁱ(-x,2-y,1-z) of 3.808 (1) Å and slipage of 1.395 and 1.865 Å, respectively, were observed.

Experimental

The titled compound (I) was synthesised by reacting hydroxybenzonitrile with bromoalkane with conventional heating (Rahman et al., 2009). Crystals of (I) were grown from hexane using a slow evaporation.